Pyridine → HCID 178462546, compound

HRID 20618Notes

Reaction equation

HRID 20618 reaction equation
[Na+:1].[CH2:2]([N+:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:10][CH:11]=2)[C:6]([CH3:24])([CH2:17][CH2:18][CH2:19][S:20]([OH:23])(=[O:22])=[O:21])[C:5]=1/[CH:25]=[CH:26]/[CH:27]=[CH:28]/NC1C=CC=CC=1)[CH3:3].[Na].[C:37]([CH2:40][CH2:41][CH2:42][C:43]1([CH3:64])[C:51]2[C:46](=[CH:47][CH:48]=[C:49]([S:52]([O-:55])(=[O:54])=[O:53])[CH:50]=2)[N+:45]([CH2:56][CH2:57][CH2:58][S:59]([OH:62])(=[O:61])=[O:60])=[C:44]1[CH3:63])([OH:39])=[O:38].N1C=CC=CC=1.CCOCC>C(O)(=O)C.C(OC(=O)C)(=O)C>[Na+:1].[Na+:1].[Na+:1].[C:37]([CH2:40][CH2:41][CH2:42][C:43]1([CH3:64])[C:51]2[C:46](=[CH:47][CH:48]=[C:49]([S:52]([OH:55])(=[O:54])=[O:53])[CH:50]=2)[N:45]([CH2:56][CH2:57][CH2:58][S:59]([OH:62])(=[O:60])=[O:61])/[C:44]/1=[CH:63]/[CH:28]=[CH:27]/[CH:26]=[CH:25]/[C:5]1[C:6]([CH3:24])([CH2:17][CH2:18][CH2:19][S:20]([OH:23])(=[O:22])=[O:21])[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([S:13]([OH:16])(=[O:14])=[O:15])[CH:8]=2)[N+:4]=1[CH2:2][CH3:3])([OH:39])=[O:38]

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 872930371-ethyl-3-methyl-2-((1E,3E)-4-phenylamino-buta-1,3-dienyl)-5-sulfo-3-(3-sulfo-propyl)-3H-indolium sodium saltHCID 874978823-(3-carboxypropyl)-2,3-dimethyl-5-sulfonato-1-(3-sulfopropyl)-3H-indolium sodium salt

Product 1

HCID 178462546HCID 178462546, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

516 mg (1 mmol) 1-ethyl-3-methyl-2-((1E,3E)-4-phenylamino-buta-1,3-dienyl)-5-sulfo-3-(3-sulfo-propyl)-3H-indolium sodium salt and 483 mg (1 mmol) 3-(3-carboxypropyl)-2,3-dimethyl-5-sulfonato-1-(3-sulfopropyl)-3H-indolium sodium salt were dissolved in a mixture of 10 ml acetic acid and 10 ml acetic anhydride followed by the addition of 5 ml pyridine. The solution was stirred under reflux for 15 min. Twenty ml ether was added after cooling to room temperature. The obtained precipitate (mixture of the diastereomers OB-5a and OB-5b) was extracted by suction, washed with ether, and dried.

Workup

  1. temperatureunder reflux for 15 min
  2. additionThe obtained precipitate (mixture of the diastereomers
  3. extractionand OB-5b) was extracted by suction
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-c135e15266414855811afd55417d53cb
Source dataset
uspto-grants-2010_06
Patent number
US07745640B2

Reaction notes

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